Jamie Herold is Hickory Hill Academy's founding Head of School.  Jamie is an enthusiastic and experienced educator and school leader with the knowledge, skills and desire to make a positive impact on a school community.  Her work as the Head of School allows her to engage with all members of the school community to create, cultivate and sustain a school environment and curriculum in which high expectations for academic and character development intersect to produce remarkable educational experiences for students, families, faculty and staff.  Jamie believes that in a thoughtful program of curriculum and instruction wonder and excitement for learning can coexist in harmony with accountability, growth and achievement.  As an educator and school leader, Jamie’s greatest strength is fostering a deep sense of community and culture. She believes that the entire student experience is born of a clear sense of feeling like a valuable member of a community, and she is thrilled to play an important role in ensuring that the community at Hickory Hill Academy is engaging, inclusive and dynamic.  


Jamie is a graduate of the University of Wisconsin, earning a B.A. in Journalism, a B.S. in Elementary Education, and an M.S. in Curriculum and Instruction.  She also holds advanced credentials in reading, working with English learners, bilingual education, and educational leadership.  Throughout her career as an educator, Jamie has enjoyed working with students in public, charter and independent school settings, most recently working at Francis Parker School in San Diego, CA.  Jamie has served as a school leader in a variety of capacities, including Department Head, chairperson for the Character Education Committee, chairperson for the Diversity, Equity and Inclusion Committee, and Curriculum Leadership Team.  Jamie is keenly familiar with many current, research-based curricular initiatives and strives to provide an innovative and comprehensive school program and a rich student experience.  Jamie practices a whole child approach to education in which the social and emotional well being of students is at the heart of teaching and learning—cultivating, supporting, and celebrating growth as students and individuals is really the work of education.


When Jamie is away from school, she enjoys baking, reading, Pilates, running, hiking, and anything active and outdoors with her family.  She is married to her college sweetheart, Randy, and they have three wonderful children, Liam, Finley and Violet.  As a family, they love to camp and explore nature.  




3276 S. High Point Road 

Madison, WI 53719

Phone: (608) 845-3245 

Email: Info@HickoryHillAcademy.com

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National Association for the Education of Young Children

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